Executive Evolution: How Great Leaders Stay Great

Three leaders shared their insights at Think., Qantas magazine’s thought leadership series that combines smart conversation with good food and wine. The panel discussion, held at Tama in Brisbane’s Fortitude Valley, was moderated by Kirsten Galliott, Head of Content, Travel and Business.

Ben Crowe

Performance and mindset coach Ben Crowe’s clients include CEOs, executives and athletes such as tennis champions Ash Barty and Dylan Alcott, surfer Stephanie Gilmore and the AFL’s Richmond Football Club. He also offers a self-development course via the Mojo Crowe app. Early in his career he parlayed his studies in philosophy, anthropology and literature into a job in sports marketing with Nike and discovered the power of storytelling.

Jennifer Child

She once dreamed of becoming a doctor but at the end of high school, Jennifer Child decided to explore other paths and joined McKinsey & Company, later becoming a partner there. In 2021, after 14 years with the firm, she was tapped to join the Oroton Group as CEO and tasked with transforming the Australian fashion and lifestyle brand, which had declared voluntary administration in 2017 after almost 80 years in business.

Craig Cowdrey

Craig Cowdrey’s background includes 10 years with the Australian Army – after officer training at the Royal Military College, Duntroon – and time as a lawyer and diplomat. He brings that diverse experience to Sonder, the wellbeing platform he co-founded in 2016 and where he is CEO. The pioneering technology company aims to make care accessible and is used by businesses and institutions across Australia, New Zealand and the UK.

I want to be the best leader I can be – where do I even start?

BEN CROWE: Leadership is creating an environment to help others realise their potential – the key word is “others”. The number one mistake leaders make is thinking that they have to have the answers and everyone’s looking at them. That’s true for doctors and lawyers but when you become a leader it has nothing to do with you and everything to do with others… to help, serve and love them, to be interested and not interesting. When it’s not about you, you can be yourself and get rid of that impostor syndrome you often see in leaders.

You work with leaders around the world. How many of them have worked out it’s about other people?

BC: The lucky ones who’ve been surrounded with good role models or have done the work on themselves are going on the hero’s journey from “I” to “we”. There are five hero hazards that hold you back from being an authentic leader – and by the way, I had all five myself. First there’s the impostor, where you feel you’re not worthy, then the rationaliser, where you make excuses and aren’t holding yourself accountable. The third is the loner, where alpha males in particular don’t ask for help or find mentors and see vulnerability as a weakness. The fourth is the glory-seeker, where you crave recognition. The fifth is the shooting star, where you achieve an enormous amount in a short time but leave a trail of destruction in terms of your family or colleagues. These are all blind spots, which means, by definition, you can’t see them without doing the work to be vulnerable and find out about yourself.

Jenny, how do you assess your own performance? Do people give you honest, unvarnished feedback?

JENNIFER CHILD: If you ask them directly, no. It’s a rare soul who can look at the CEO and say, “I’ve got some feedback for you.” I don’t think it’s always constructive. There are tools you can use, such as the 360 degree feedback mechanism, where people are anonymous so feel more comfortable to share what they see you need to improve on. It’s important to use those tools and at Oroton, I quickly found a small group of trusted people who I know will tell me the truth because they care about me. That’s a special thing and you have to allow those people to share things with you that you might not want to hear.

Craig, you’re a co-founder and CEO. Are your co-founders willing to tell you what sort of day you’re having?

CRAIG COWDREY: The position of CEO is often quite lonely but co-founders can speak more openly to you – whether you want them to or not. When you transition from individual contributor to manager to leader, it becomes about fostering an environment in which people can thrive. I seek out feedback from my chair, the co-founder who’s still working in the business and the executive team. I bring tools from previous careers, including the after action review or AAR from the Army, which I’m sure many do. It’s about: something’s occurred then you delve deeply into why it occurred by doing a retrospective immediately after to reflect on what you can sustain, what you can improve and what you can fix. We do AARs in our business and I also do them for myself, going through the exercise by writing it down before a board meeting.

Ben, you talk about the importance of celebrating our imperfections. Why is that important?

BC: We’re just so friggin’ hard on ourselves as a human race. We’ve got this reptilian brain with a negative bias – it’s Velcro for negative and Teflon for positive. We all need to do what they say on Ted Lasso, “Get some scissors and cut yourself some slack.” Perfectionism is caring what other people think about you and trying to live up to this perfect image. When you go the other way and accept your imperfections, it links to authenticity – “This is who I am, how I was born, and these are the cards I’ve been dealt.” We call it embracing your weird. Celebrating imperfections leads to acceptance of who you are but we suck at acceptance because we compare and judge ourselves. Acceptance is a skill and once you realise you can develop and build this acceptance muscle, it can be a competitive advantage.

Are you comfortable showing vulnerability at work, Jenny?

JC: You’d have to ask other people but I talk about my mistakes all the time. I say, “I screwed that one up”, discuss why it wasn’t as good as it could have been, what I’d do differently next time and get feedback. Oroton is an 86-year-old business that came out of administration not that long ago so we’re taking the whole thing and putting it on its head and changing the way we work at a fundamental level. To do that, you need a test-and-learn mindset and culture and to say openly, “No-one’s getting persecuted, we’re trying to learn.” It has to start with the thing that didn’t go right. Getting what went wrong to come out is a challenge – most people aren’t comfortable with that.

You spent 14 years at McKinsey, which has a focus on strategy. What do you rely on most in your problem-solving toolkit?

JC: Lots of frameworks! The toolkit you get at a place like McKinsey is how to take any complex problem – across industries and across functions – and tear it down to its parts so you can analyse it and build up to an answer. That toolkit is going to be with me for the rest of my life and I’m really thankful for that. I can come into a place like Oroton and look at where we are today – not the business we want to be. That’s the first thing I did when I came in: understanding all the parts of what Oroton was at that point and figuring out a way forward.

Craig, when you look back at your career – the law, military, diplomacy – what have you taken from each that’s made you the leader you are today?

CC: Teamwork is a critical part of the Army – it’s hierarchical but I learnt to play my role in the team. You needed to be open to ideas but once the debate had been had and the decision made – whether by you, the commanding officer or whoever – you execute the decision as if it’s your own. No hesitation, no second-guessing, no undermining. If you didn’t agree with it, you’ve had your chance, now carry it out. In law, I learnt that the precision of communication is so important – spend time and money getting the language right at the front end of a deal and you’ll save time down the road. In diplomacy, I was at the UN Security Council in New York for a couple of years and Hong Kong after that. At the start, I brought my corporate law hat. Then I realised that when you’re dealing with other diplomats, trade officials, you have to let your genuine self out. Don’t be purely transactional and you’ll get a better response. At the end of the day, it’s humans dealing with humans and you might be negotiating a free-trade agreement or whatever it may be but you have to be your authentic self and let character into those interactions, rather than be mechanical.

Continuous learning is so important. Jenny, I know you listen to a lot of podcasts, including Making Sense with Sam Harris. What have you applied from that?

JC: Sam Harris talks about the importance of understanding that death is inevitable for all of us and if you can embrace that concept, you can appreciate your life. It’s about having the ability to live in the moment and acknowledge the hard stuff as well as the great stuff. That’s really shaped my leadership. Being able to talk about it helps other people to open up and appreciate what they’re doing, even on the crappy, hard days.

BC: Bronnie Ware is a beautiful Australian hospice nurse who wrote a book 10 years ago called The Top Five Regrets of the Dying. You know, I wish I hadn’t worked so hard. I wish I’d spent more time with friends. I wish I’d showed my emotions more. I wish I’d allowed myself to be happy. But the number one deathbed regret all over the world is: I wish I’d lived a life true to myself and had the courage to be me, rather than the life others expected of me. I think that’s the biggest.

Craig, is it true that you like to really immerse yourself in learning?

CC: Everyone’s busy so it’s hard to go deep on a particular topic. My way of doing it is blocking out time for maybe three or four hours and locking myself in a room. For example, a couple of months ago I spent three hours deep-dive learning about generative AI then another three hours thinking about how we could apply it at Sonder. It’s in the third hour that the epiphanies come. It was really useful for me.

BC: We all learn in different ways and we’re all at different stages in those journeys, tapping into that curiosity and being open-minded about finding mentors or other people you can learn from. These mentors don’t even have to be real. For me, [late American comic] Robin Williams is one of my mentors, another is Ted Lasso and also my dad. He has passed away but when I’m going through a tricky time, I’ll often say, “What would my dad do in this situation?”

Jenny, you work with a coach, don’t you?

JC: When I left McKinsey, I found a coach who actually came from the company so he understands that part of me and strategy really well. If I’m stuck on something that I know is the strategic direction I want the business to move in but it’s not moving fast enough, talking with him about how to build momentum has been a real asset.

You also have a therapist, which is equally important to you.

JC: I’ve had a therapist since my early 20s. Understanding the depths of who I am as a human being, combined with what I’m trying to do with the business is a great combination. Every day I can come into a meeting and shape the way someone feels about the work they’ve done. I try to show up as the best version of myself and I think it takes dual things – the coach and the therapist – to get there.

CC: I have four or five investors and advisors who I go to with specific issues but I’m thinking I need a more structured approach. One of the things we test for when we recruit people is their ability to be self-aware and autonomous and there are certain questions we ask to try to identify that in candidates.

Craig, you aim to identify self-awareness when you’re recruiting. How do you do that?

CC: We have a “hire slow, fire fast” approach. If you hire people who are the wrong fit, it’s very difficult for everyone involved so we put a lot of work into making sure we articulate the skills matrix and are transparent about the business. I like to ask, “You’ve been really successful in your career. What are the three things you attribute that to?” If the candidate says, “I’m smart, hardworking and resilient,” then maybe that’s okay but what I really prefer to hear is that they point to something outside of themselves. They might say, “Well, I was lucky, I had a great mentor in school and she inspired me to get into software coding,” or perhaps, “My dad was a doctor in the Middle East and now he cleans toilets here – he sacrificed everything to give me this chance.” I’m not a psychologist but I’ve found that those kinds of answers indicate an awareness that none of us does this on our own. We all have someone who helps us and people who push us forward. If you think it’s all you then you’re probably not very self-aware.

BC: We’ve got a very different approach: we ask people if they like Ted Lasso. If they don’t, we don’t hire them and if they do, we ask them which character they like the most. That’s the conversation where we pick up their self-awareness. It’s not that mature, I admit!

What’s one pivotal moment that defines your leadership style?

CC: As a new lieutenant out of Duntroon, the first job they give you is leading the battery – 20 to 30 vehicles, six artillery pieces – through the bush. Six days into the exercise we went down a wrong path in the middle of the night. The commanding officer stopped the convoy and said, “Lieutenant Cowdrey, what happened?” And I said, “Sir, this sergeant took us over this fence and into barbed wire.” He pulled me aside and said, one-on-one, “I don’t ever want to hear you blame one of your soldiers again… as a leader, you take blame and you give credit. Your job is to protect these men, not throw them under the bus.” I was a deer in the headlights, absolutely floored, and it’s always stuck with me. He became a great mentor to me.

Things like that do stay with you, don’t they, Ben?

BC: On a similar theme, when I was working at Nike I was trying to sign the All Blacks – they were the crème de la crème of rugby – and I’d stuffed up the negotiations to some degree. It was one of the biggest deals that I missed out on but my boss blamed his leadership for the loss. I didn’t even know him that well. Afterwards I said, “I made those mistakes; you didn’t.” He said, “I know that but it’s my responsibility.” I have never forgotten that lesson – the responsibility of protecting your people.

JC: Early in my career at McKinsey, I was in my 20s, still getting my feet under me, but I had a few good runs. A project manager said to me, “I’ve staffed you on this project – I’ve heard you’re a rock star so let’s see.” It was so aggressive and shook me. It was in telco, a whole new sector for me. On the first day, I was pacing out the front of the client’s building and didn’t want to go in because I was so nervous. My mentor was a senior partner at McKinsey who’d said to me, “If you ever need a pep talk, call me,” and I thought, “Okay, this is the moment.” He told me about when he was at the same stage in his career and had a big failure – and now he was one of the most senior people in the company. The moral was: the worst-case scenario is you’ll suck at this project but so what? He told me it was a good thing I was nervous – it means you’re going to be better. My brain shifted into gear. Now when I get nervous I lean in: “Oh, this is gonna be good!” I use it as a coaching tool for younger people – how nerves are fuel, not something to be scared of.

Final Thoughts...

On taking control of your calendar

“I embrace two truths about time – it’s finite and not all time is created equal. I have a mental model about my calendar. The principle is there are important topics that need priority and attention in any given week – those are the big rocks. Then you have the pebbles and sand. If you fill up your jar with the rocks first, the pebbles and sand can fill in around it. But if the sand goes in first, it’s too hard to push the rocks in. It’s a simple theory about being in control of how I spend my time versus my calendar being in control of me.” — JENNIFER CHILD

On keeping ambition in perspective

“I don’t have a client on the planet – from Ash Barty to top CEOs – who isn’t obsessed with achieving their goals and dreams. I love the focus on and intent to do everything in your power to chase that – as long as you don’t determine your self-worth by whether you win or lose because you can’t control that. If you define your success purely by winning, does that mean you’re a failure if you don’t win?” — BEN CROWE

On striking a delicate balance

“There’s an appropriate level of vulnerability but people want their leaders to know what they’re doing. They don’t want to think, ‘Oh, my God, this person has no idea and no strategy.’ If there’s uncertainty, you need a level of decisiveness and the leader to say, ‘We’re going over here.’ There’s an old expression in the Army that says leaders never run anywhere because it scares the troops. You walk calmly, talk calmly, be confident.” — CRAIG COWDREY

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Our next Think. event will be in Melbourne on Monday, 18 November 2024.

For more information, enquire at rsvp@mediumrarecontent.com

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